Acetone → 6-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

HRID 268404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268404
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([O:18]C)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].CC(C)=O.Cl>O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 144156636-Acetoxy-2-methoxy-2,5,7,8-tetramethylchroman

Produkt 1

HCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (±)-6-acetoxy-2-methoxy-2,5,7,8-tetramethylchroman in 2500 ml. of acetone was added 2000 ml. of H2O followed by 16.6 ml. of concentrated aqueous HCl. Solvent was distilled from the stirred mixture until the head temperature reached 90°C. The suspension was cooled in an H2O bath to 50°C. At 70°C., 2000 ml. of acetone was added, giving a clear solution. The solution was seeded occasionally until crystallization began. After 3.5 hours, 1500 ml. of H2O was added and the suspension was cooled in an ice bath. The solid was removed by filtration, washed with H2O and dried at 50°C./0.1 mmHg. to give (±)-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman as a granular yellow-tan solid, sintering from 114°C., m.p. 127°-132°C.

Aufarbeitung

  1. distillationSolvent was distilled from the stirred mixture until the head temperature
  2. customreached 90°C
  3. customAt 70°C.
  4. additionof acetone was added
  5. customgiving a clear solution
  6. customThe solution was seeded occasionally until crystallization
  7. additionof H2O was added
  8. temperaturethe suspension was cooled in an ice bath
  9. customThe solid was removed by filtration
  10. washwashed with H2O
  11. customdried at 50°C./0.1 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-9b01473f7d844bd992f6974962afc07c
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03947473

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